Work-It Girl

In fashion, as in life, you can't win if you don't play

There's this great Samuel Beckett quote I like to repeat to myself in a fired-up, Oprahwould- high-five-me kind of way: "Ever tried, ever failed, no matter. Try again. Fail again. Fail better." It's that last part with its catchy cadence that I make my mantra as I pretend that's the kind of person I am: out on a limb, tireless, fearless, unencumbered by expectations. No shame: There's honor in failure! Fail better! Make it count!

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But while the kind of person who busts out that quote and means it is who I want to be, it's not who I am. When doubt creeps in and I suspect I don't have what it takes to pull something off, I'm not noble or poetic. I'm altogether resistant. And when it comes to my wardrobe... check, please.

As a kid, I loved fashion for its glamour and otherworldliness—the same reason I wanted to be She-Ra, Princess of Power—but neither ever struck me as attainable. College was Northwestern's journalism school, where conspicuously doing crossword puzzles in pen counted as flirtation and fashion was synonymous with fleece.

So after landing, somewhat inexplicably, at a fashion magazine, I was relieved that jeans trumped business suits, but oh, how new I was. To wit, jeans are not just jeans—there's an ever-changing right color and cut. And if you thought working mostly with women is like a slumber party where you show up unshaven and sporting flannel— wrong again. Close up, fashion isn't a fantasy but a business, a precarious enterprise with distinct seasons and even more distinct faux pas.

So I followed the mellow brick road all the way to smug and said: I give up. I won't risk ending up a fashion hamster—exhausting myself trying, never quite pulling it off—but I will always, always know where the comma goes. And the rest of you label-obsessed waist-cinchers and foot-pain-bearers can work at looking strut-worthy, but no way can you spell carburetor or kick my ass in Scrabble. Right?

The fashion-industry reality, however, is that your look is an endorsement of your own ambition: Anything goes, but everyone notices. And anyone who's failing better than me is also more likely to succeed.

If this is all starting to sound like the fashion identity crisis in The Devil Wears Prada, well, it is. In the movie, you'll remember, Anne Hathaway's Andy Sachs is forced to realize that her aversion to fashion isn't helping her career or life; fashion is art, expression, an industry born of innovation but constantly feeding on history; all this frivolous nonsense is anything but.

That's where the similarities end. Andy hails from Hollywood, where a magazine's fashion closet is a free-for-all and pivotal transformations are set to pop music and take three and a half minutes. Here in the real world, my salary hardly covers breakfast, let alone a wow-inducing wardrobe. A metamorphosis like Andy's wouldn't take a pop song; it would take a village.

Enter the battalion: Seth, the label lover who dismisses all my shoes as "orthopedic sandals"; Annie, spewer of diplomatic lines like, "You have your own thing going— that's cool!"; and Jade, the market editor for whom black is always the new black.

The goal: to wrestle me out of my loose cottons and tap into the potential they saw that I always felt too intimidated to explore. They got me into a Banana Republic short print dress and vintage motorcycle jacket (this passes as professional garb—believe it!), but I soon found out that these were merely an homage to the shoes: Christian Louboutin black patent leather six-inch spiked heel platforms. "I always dress from the shoe up," Jade told me as I stuffed my cowering feet into those twin peaks of glamour. Or is it torture? After an hour, I thought I needed X-rays.

But they were magnificent. I felt a bit like an impostor, but I also felt smarter, not just sexier. I walked differently: In shoes like those, you must focus on every step, as if learning the tango. The confidence of your own swagger seduces you.

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I swaggered into our editorial meeting that morning, and the reaction was instant. Shock mixed with shock. Some asked me if I was going on interviews. Others used words like sex bomb and awesome. In the lobby, the security guard—who each day acts like he's never seen me before and makes me rifle through my bag for my ID as I murmur, "Two and a half years...you've got to be kidding me"—said nothing but "You look nice," and waved me through.

All day, I had the feeling I belonged wherever I was—and a subsequent pang of despair that maybe the "impostor" was who I was yesterday, the girl masquerading in the baggy jeans and orthopedic sandals.

The next day, Seth was beaming. "We got you some skinny jeans." Ah, yes—the "right" kind.

"No!" I protested. "Uh-uh. No. I draw the line at those...things."

Skinny jeans, with their '80s tapered leg and overdose of spandex, are a trend I've avoided to the point of anger. They perfectly embody why I shun trends in the first place: Not only are you obviously trying, but you're trying to look like everyone else! But Seth wouldn't leave until I sucked it up, sucked it in, and pulled on the jeans, all the while thinking (1) I have blatantly sold out, and (2) Is that my butt? Wow. "Something weird is happening to me," I said, as Seth rolled his eyes as if to say, Finally. "Don't tell anyone," I whispered, "but I never want to take these off." And then: "Please don't make me give them back."

That night, I met up with Rachel, an old friend who's been forever plagued by gorgeousness and charm. She's never met a boy who didn't start out lust-struck and end up tormented. I wore the jeans, wore the shoes, did my hair, put on makeup. Nothing was going to show up her effervescence, but it's about trying, right? Failing better.

The entire night, I could barely blink without attracting another hovering guy. I don't know if it was the jeans, but—no, I know it was the jeans. I don't know for sure that it was the way they looked, but I do know for sure that it was the way I felt.

Back at home, I wondered why I had always been so wary of caring too much, trying too hard. For one thing, it's the fear that dressing to impress is announcing, "I've scoured my brain, my very soul, and it turns out that this is all I've got going for me." But why am I worrying about someone else's ability to see past my cocktail ring? Isn't that ultimately their problem?

There's one thing that all women know, though many of us worry we'll be crucified for admitting it in a postfeminist world: Turning heads is a bona fide high that never, ever gets old. And if I beat myself up for chasing that high, I'm making it more important than a pair of heels ever could. Christian Louboutin never hurt anyone.